Fe(OTf)3-Catalyzed Synthesis of Boronic Ester Containing N,O-Acetal Structure

doi:10.6023/cjoc202301017

Abstract

A convenient approach acess to boronic ester containing N,O-acetal structure has been established through the Fe(OTf)₃-catalyzed addition of N,O-acetal with organic boric acid. A series of N-O-acetal boronic ester compounds have been successfully prepared in 58%~98% yields. Moreover, these compounds retain the property of boronic ester and can be used for coupling reaction.

Key words: iminonium, N,O-acetal, boronic ester, addition reaction

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Min Lü, Aimei Yang, Yu Zhang, Jianting Sun, Bangguo Wei. Fe(OTf)₃-Catalyzed Synthesis of Boronic Ester Containing N,O-Acetal Structure[J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1777-1785.

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Fig. & Tab. 7

References 16

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Entry^a	Additive (equiv.)	Solvent	Yield^b/%	dr^c
1^d		DCM	Trace
2^e		DCM	NR
3	K-10	DCM	Complex
4	TMSOTf (1.0)	DCM	Complex
5	TMSOTf (0.2)	DCM	NR
6	BF₃•Et₂O (0.2)	DCM	30	>99∶1
7	Ce(OTf)₄ (0.2)	DCM	20	>99∶1
8	Pr(OTf)₃ (0.2)	DCM	35	>99∶1
9	Dy(OTf)₃ (0.2)	DCM	39	>99∶1
10	Tm(OTf)₃ (0.2)	DCM	32	>99∶1
11	Yb(OTf)₃ (0.2)	DCM	33	>99∶1
12	Sc(OTf)₃ (0.2)	DCM	50	>99∶1
13	Ni(OTf)₃ (0.2)	DCM	49	>99∶1
14	Zn(OTf)₂ (0.2)	DCM	41	>99∶1
15	Cu(OTf)₂ (0.2)	DCM	51	>99∶1
16	In(OTf)₃ (0.2)	DCM	34	>99∶1
17	AuCl₃/AgSbF₆ (0.2)	DCM	33	>99∶1
18	Fe(OTf)₃ (0.2)	DCM	81	>99∶1
19	Fe(OTf)₃ (0.2)	THF	65	>99∶1
20	Fe(OTf)₃ (0.2)	DCE	78	>99∶1
21	Fe(OTf)₃ (0.2)	DMF	60	>99∶1
22	Fe(OTf)₃ (0.2)	Toluene	NR
23	Fe(OTf)₃ (0.1)	DCM	90	>99:1
24	Fe(OTf)₃ (0.05)	DCM	58	>99:1

Entry^a	Additive (equiv.)	Solvent	Yield^b/%	dr^c
1^d		DCM	Trace
2^e		DCM	NR
3	K-10	DCM	Complex
4	TMSOTf (1.0)	DCM	Complex
5	TMSOTf (0.2)	DCM	NR
6	BF₃•Et₂O (0.2)	DCM	30	>99∶1
7	Ce(OTf)₄ (0.2)	DCM	20	>99∶1
8	Pr(OTf)₃ (0.2)	DCM	35	>99∶1
9	Dy(OTf)₃ (0.2)	DCM	39	>99∶1
10	Tm(OTf)₃ (0.2)	DCM	32	>99∶1
11	Yb(OTf)₃ (0.2)	DCM	33	>99∶1
12	Sc(OTf)₃ (0.2)	DCM	50	>99∶1
13	Ni(OTf)₃ (0.2)	DCM	49	>99∶1
14	Zn(OTf)₂ (0.2)	DCM	41	>99∶1
15	Cu(OTf)₂ (0.2)	DCM	51	>99∶1
16	In(OTf)₃ (0.2)	DCM	34	>99∶1
17	AuCl₃/AgSbF₆ (0.2)	DCM	33	>99∶1
18	Fe(OTf)₃ (0.2)	DCM	81	>99∶1
19	Fe(OTf)₃ (0.2)	THF	65	>99∶1
20	Fe(OTf)₃ (0.2)	DCE	78	>99∶1
21	Fe(OTf)₃ (0.2)	DMF	60	>99∶1
22	Fe(OTf)₃ (0.2)	Toluene	NR
23	Fe(OTf)₃ (0.1)	DCM	90	>99:1
24	Fe(OTf)₃ (0.05)	DCM	58	>99:1

Fe(OTf)₃催化含有N,O-缩醛结构硼酸酯的合成研究

Fe(OTf)₃-Catalyzed Synthesis of Boronic Ester Containing N,O-Acetal Structure

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Fe(OTf)3催化含有N,O-缩醛结构硼酸酯的合成研究